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Topic: Why the only one product is made?  (Read 3464 times)

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Offline plankk

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Why the only one product is made?
« on: July 07, 2011, 05:00:56 AM »
http://nernst.chem.metu.edu.tr/icho2011/files/IChO2011%20Prep%20problems%20with%20solutions%20110215.pdf  (page 80)

I tried to do on my own task 29 however I have no idea why in products B1 and B2 both substituents are cis. I suppose that they will be rather trans. Is there any kind of model (like Felkinh-Anh) which is able to explain it?

Offline discodermolide

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Re: Why the only one product is made?
« Reply #1 on: July 07, 2011, 06:57:07 AM »
http://nernst.chem.metu.edu.tr/icho2011/files/IChO2011%20Prep%20problems%20with%20solutions%20110215.pdf  (page 80)

I tried to do on my own task 29 however I have no idea why in products B1 and B2 both substituents are cis. I suppose that they will be rather trans. Is there any kind of model (like Felkinh-Anh) which is able to explain it?

Looks like a 2+2 cycloaddition to me, which gives the cis beta lactam
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Offline AlbertoA

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Re: Why the only one product is made?
« Reply #2 on: July 07, 2011, 07:09:31 PM »
here's a stupid question, Problem 27 part c
Why do the cyclohexa 1,3- diene gives only one product when 1 equivalent of mCPBA, wouldn't t produce a racemic mixture?

Offline BluePill

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Re: Why the only one product is made?
« Reply #3 on: July 07, 2011, 10:20:07 PM »
It's just the same molecule even if you flip it.

Offline AlbertoA

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Re: Why the only one product is made?
« Reply #4 on: July 07, 2011, 10:49:22 PM »
aaaaaa!! yes!!! My bad  :( :( :( :(

Offline orgopete

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Re: Why the only one product is made?
« Reply #5 on: July 07, 2011, 11:06:39 PM »
here's a stupid question, Problem 27 part c
Why do the cyclohexa 1,3- diene gives only one product when 1 equivalent of mCPBA, wouldn't t produce a racemic mixture?

I agree with you. The product shown is a 1R,2S. There is no reason a 1S,2R product should not also accompany it.
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